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Amino acid polypyridyl copper complex and preparation method and application thereof

A technology of copper complexes and amino acids, applied in copper organic compounds, pharmaceutical formulations, organic chemical methods, etc., can solve the problems of limited clinical wide application, toxic and side effects, severe drug resistance, etc., and achieve good anticancer activity and preparation method. simple effect

Pending Publication Date: 2017-06-23
天津市医药科学研究所
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, since the target is DNA, the lack of selectivity to tumor cells leads to great gastrointestinal and blood side effects. In addition, cisplatin cannot be taken orally and has serious drug resistance, which limits its wide clinical application.

Method used

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  • Amino acid polypyridyl copper complex and preparation method and application thereof
  • Amino acid polypyridyl copper complex and preparation method and application thereof
  • Amino acid polypyridyl copper complex and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Synthesis of copper complex 1:

[0032] Dissolve 0.5mmol of amino acid and 0.5mmol of alkali in 20mL of water and 20mL of alcohol mixed solution, add 0.5mmol of copper chloride under stirring at room temperature, reflux and stir for 3 hours, filter, add 0.5mmol of ammonium hexafluorophosphate, and continue the reaction at room temperature After 1 hour, filter, and the filtrate evaporates slowly at room temperature. After 3 weeks, green crystals suitable for X-ray analysis are precipitated, and the yield is about 48% (calculated as copper salt). Elemental analysis results (%), experimental value: C, 54.80; H, 4.62; N, 11.40. Theoretical value (C 28 h 28 N 5 o 5 ClCu): C, 54.81; H, 4.60; N, 11.41, the results are basically consistent with the theoretical value.

Embodiment 2

[0034] Synthesis of copper complex 2:

[0035] Dissolve 0.5mmol of amino acid and 0.5mmol of base in 20mL of 1 water and 20mL of alcohol mixed solution, add 0.5mmol of copper nitrate under stirring at room temperature, reflux and stir for 3 hours, filter, add 0.5mmol of ammonium hexafluorophosphate, and continue the reaction at room temperature for 1 hour, filtered, and the filtrate was slowly volatilized at room temperature. After 3 weeks, a green crystal suitable for X-ray analysis was separated out, and the yield was about 41% (calculated as copper salt), elemental analysis result (%), experimental value: C, 44.54; H, 3.95; N, 14.85. Theoretical value (C 21 h 22 N 6 o 9 Cu): C, 44.56; H, 3.92; N, 14.85. The results are basically consistent with the theoretical value.

Embodiment 3

[0037] Synthesis of copper complex 3:

[0038] Dissolve 0.5mmol of amino acid and 0.5mmol of alkali in 20mL of water and 20mL of alcohol mixed solution, add 0.5mmol of copper chloride under stirring at room temperature, reflux and stir for 3 hours, filter, add 0.5mmol of ammonium hexafluorophosphate, and continue the reaction at room temperature After 1 hour, filter, and the filtrate evaporates slowly at room temperature. After 3 weeks, green crystals suitable for X-ray analysis are precipitated, and the yield is about 43% (calculated as copper salt). Elemental analysis results (%), experimental value: C, 52.90; H, 3.65; N, 14.01. Theoretical value (C 22 h 18 N 5 o 3 ClCu): C, 52.91; H, 3.63; N, 14.02, the results are basically consistent with the theoretical value.

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Abstract

The invention relates to an amino acid polypyridyl copper complex and a preparation method and application thereof. Chemical formulas are respectively [Cu(OH-PIP)(Phe)Cl] 3H2O (1), [Cu(OH-PIP)(Gly)(H2O)]NO3 2H2O (2), [Cu(OH-PIP)(Ala)(Cl)] (3), [Cu(OH-PIP)(Met)]n(PF6) 2H2O (4) and [Cu(OH-PIP)(Gln)(H2O)](Cl) 3H2O (5), wherein OH-PIP is 4-(1-hydro-imidazole[4,5-f][1,10]phenanthroline-2-xyl)phenol, Phe is phenylalanine, Gly is glycine, Met is methionine, Ala is alanine, and Gln is glutamine. After the anti-tumor activity of MCF-7, SMMC-7721, K562, A549 and SGC-7901 cells is evaluated by an MTT method, the amino acid polypyridyl copper complex is found to have the advantages that the good anti-cancer activity on the cells is good, the certain inhibiting function on the activity of proteasome is realized, and the amino acid polypyridyl copper complex can be used as a targeting anti-cancer drug with potential application value.

Description

technical field [0001] The invention relates to a preparation method and application prospect of an amino acid polypyridine copper complex. The complex has good anticancer activity on selected tumor cell lines and has a certain inhibitory effect on proteasome activity, so it can be used as A proteasome-targeted antitumor or anticancer drug with potential application value. Background technique [0002] Cancer is a general term for a large class of malignant tumors and is one of the most important diseases threatening human life. In the late 1960s, cisplatin, with its excellent anti-tumor effect, led the scientific community to further in-depth research on the pharmacological functions of metal complexes. Subsequently, many new metal complexes with high efficiency, low toxicity and anticancer properties have been continuously synthesized and gradually put into clinical application. Among them, platinum-based antitumor drugs such as cisplatin and carboplatin have become the ...

Claims

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Application Information

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IPC IPC(8): C07F1/08A61K31/555A61P35/00
CPCC07B2200/13C07F1/005C07F1/08
Inventor 李冬冬陶遵威赵秀梅顾娜郑夺
Owner 天津市医药科学研究所
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